Like Clockwork: 40 Years of Ice-Cold Psychopaths

Forty years ago, a derby-capped, Beethoven-loving English hoodlum smashed noggins with so much style that he set a new benchmark for psychopathic behavior.

After Alex and his Droogs wreaked havoc in 1971's A Clockwork Orange, ambitious filmmakers could no longer get by with standard-issue bad guys. Stanley Kubrick's adaptation of novelist Anthony Burgess' futuristic satire impacted Hollywood-style depravity: Audiences would now expect extra dollops of wit and cruelty from their bad guys. And if the psycho wore a creepy mask or really bad haircut, all the better.

To mark the 40th anniversary of A Clockwork Orange, which will be re-released Tuesday on Blu-ray, Wired.com chronicles the spawn of Alex with a gallery of the sickest, coldest and most charismatic evil bastards from the past four decades of movie history.

Mr. Big

Psycho factor:Yaphet Kotto, as sadistic mastermind Mr. Big, predates torture porn by decades when he instructs his aide Tee Hee: "On the first wrong answer from Miss Solitaire, you will snip the little finger of Mr. Bond's right hand. Starting with the second wrong answer, you will proceed to the more ... vital ... areas."

Mr. Big

Psycho factor:Yaphet Kotto, as sadistic mastermind Mr. Big, predates torture porn by decades when he instructs his aide Tee Hee: "On the first wrong answer from Miss Solitaire, you will snip the little finger of Mr. Bond's right hand. Starting with the second wrong answer, you will proceed to the more ... vital ... areas."

Nurse Ratched

Psycho factor: Dealing with Jack Nicholson's rebellious Randle McMurphy, mental hospital matron Nurse Ratched says, "If Mr. McMurphy doesn't want to take his medication orally, I'm sure we can arrange that he can have it some other way." Uh oh. Louise Fletcher wins an Oscar for her portrayal of a bureaucratic monster who believes in control-through-sedation.

Michael Myers

Psycho factor: A 6-year-old murders his older sister, escapes the loony bin and freaks the daylights out of Jamie Lee Curtis' character, thus launching a nine-movie franchise. Filmmaker John Carpenter invented Michael Myers, played by Nick Castle and Tony Moran in this first installment, after taking a college field trip to a Kentucky mental institution. A 12-year-old patient gave the director a "a real evil stare" that Carpenter remembers as being "completely insane."

Jack Torrance

Psycho factor: Stanley Kubrick's cinematic adaptation of Stephen King's chilling novel is filled with carefully composed visuals and literary allusions. But the film's most iconic moment is improvised by Jack Nicholson when his Jack Torrance character bursts through a door, ax in hand, and announces, "Here's Johnny!"

Roy Batty

Psycho factor: Unstoppable Rutger Hauer, playing the relentless Roy Batty in Ridley Scott's sci-fi stunner, shows what he's made of when he pulls the hand belonging to Harrison Ford's Deckard through the wall, then breaks two of his fingers, proving that good characters do bad things.

Roy Batty

Psycho factor: Unstoppable Rutger Hauer, playing the relentless Roy Batty in Ridley Scott's sci-fi stunner, shows what he's made of when he pulls the hand belonging to Harrison Ford's Deckard through the wall, then breaks two of his fingers, proving that good characters do bad things.

Tony Montana

Psycho factor: Spewing cocaine-fueled rants while dressed in tailor-made suits, Al Pacino transforms a Miami drug dealer into an antihero for the ages when he greets cops by unveiling ridiculously large weapons and shouting, "Say hello to my little friends!"

Tony Montana's vivid dialog, scripted by Oliver Stone, also includes such stingers as, "Why don't you try sticking your head up your ass? See if it fits," and "Orders? You giving me orders? Amigo, the only thing in this world that gives me orders is balls. You got that? Balls!"

Tony Montana

Psycho factor: Spewing cocaine-fueled rants while dressed in tailor-made suits, Al Pacino transforms a Miami drug dealer into an antihero for the ages when he greets cops by unveiling ridiculously large weapons and shouting, "Say hello to my little friends!"

Tony Montana's vivid dialog, scripted by Oliver Stone, also includes such stingers as, "Why don't you try sticking your head up your ass? See if it fits," and "Orders? You giving me orders? Amigo, the only thing in this world that gives me orders is balls. You got that? Balls!"

Freddy Krueger

Psycho factor: Fedora + knife glove + Robert Englund = horror legend. A generation of young moviegoers lose sleep after Wes Craven introduces them to the creep in the red-striped sweater who kills people — including Johnny Depp's character in this first of nine Nightmare films — while they're dreaming.

Frank Booth

Psycho factor: What the hell? Dennis Hopper's creepy scumbag inhales amyl nitrite and exhales feral menace each time director David Lynch points the camera at him. Frank Booth is living proof that perverts might just be living next door in Anytown, USA.

Clarence J. Boddicker

Psycho factor: Just before Officer Alex J. Murphy gets gunned down by weaselly crime boss Boddicker, played by Kurtwood Smith in Paul Verhoeven's classic sci-fi film, the man who will become RoboCop sums up the audiences' sentiments with precision: "Buddy, I think you're slime."

Hans Gruber

Psycho factor: Opposite Bruce Willis in John McTiernan's action franchise opener, Alan Rickman's crisp kidnapper Hans Gruber addresses hostages with one of many great lines: "I wanted this to be professional. Efficient, adult, cooperative, not a lot to ask. Alas, your Mr. Takagi did not see it that way, so he won't be joining us for the rest of his life."

Early Grayce

Psycho factor:Brad Pitt is all good ol' boy smiles and zero remorse in his unsettling turn as an escaped convict who travels cross-country with his terrorized girlfriend (Juliette Lewis). In director Dominic Sena's thriller, Early Grayce rapes women, beats David Duchovny's character and kills an elderly man without so much as a wrinkled brow while drawling out lines like, "Ya better watch it Bri, 'cuz it's comin'."

Early Grayce

Psycho factor:Brad Pitt is all good ol' boy smiles and zero remorse in his unsettling turn as an escaped convict who travels cross-country with his terrorized girlfriend (Juliette Lewis). In director Dominic Sena's thriller, Early Grayce rapes women, beats David Duchovny's character and kills an elderly man without so much as a wrinkled brow while drawling out lines like, "Ya better watch it Bri, 'cuz it's comin'."

Jules Winnfield

Psycho factor: The Bible-quoting hit man, played by Samuel L. Jackson , delivers the gospel according to Tarantino when he quotes scripture on the killing floor: "There's this passage I got memorized. Ezekiel 25:17: 'The path of the righteous man is beset on all sides by the inequities of the selfish and the tyranny of evil men.'"

Jules Winnfield

Psycho factor: The Bible-quoting hit man, played by Samuel L. Jackson , delivers the gospel according to Tarantino when he quotes scripture on the killing floor: "There's this passage I got memorized. Ezekiel 25:17: 'The path of the righteous man is beset on all sides by the inequities of the selfish and the tyranny of evil men.'"

John Doe

Psycho factor:Kevin Spacey plays a high-concept serial killer drawing from the Seven Deadly Sins playbook. When John Doe decapitates Gwyneth Paltrow's character and delivers the head in a box, that's evil.

Ghostface

Psycho factor: It's the shrieking mask, not the actors wearing it, that give this character enduring power. In this initial chapter of the horror franchise, Skeet Ulrich and Matthew Lillard don the disturbing costume during a killing spree in the fictional town of Woodsboro, California.

Jean-Baptiste Emanuel Zorg

Psycho factor: Intense British thespian Gary Oldman gets styled with the lankiest forelock in movie history for his role in Luc Besson's visually rich sci-fi movie, in which the evil Zorg spits out lines like this: "Life, which you so nobly serve, comes from destruction, disorder and chaos."

Jean-Baptiste Emanuel Zorg

Psycho factor: Intense British thespian Gary Oldman gets styled with the lankiest forelock in movie history for his role in Luc Besson's visually rich sci-fi movie, in which the evil Zorg spits out lines like this: "Life, which you so nobly serve, comes from destruction, disorder and chaos."

Severus Snape

Psycho factor:Alan Rickman, king of the British villains, sets the table for Ralph Fienne's wicked Lord Voldemort a few movies later by generating clouds of doom as the greasy-haired sourpuss intent on vexing Harry Potter.

Green Goblin

Psycho factor: Lanky Willem Dafoe cackles his way through the Green Goblin's revenge story by sticking to this statement of purpose: "To say what you won't, to do what you can't, to remove those in your way."

Vernita Green

Psycho factor: When The Bride (played by Uma Thurman) comes calling on Vernita, played by Vivica A. Fox, the assassin-turned-suburban-hausfrau goes for broke in the best knife fight involving boxes of Captain Crunch ever.

Dr. Jonathan Crane, aka The Scarecrow

Psycho factor: He's a doctor. He's a sadist. He's a doctor. He's a sadist. Cillian Murphy plays the split-personality card perfectly as a mad scientist who throws a bag over his own head and forces victims to hallucinate their worst fears.

Anton Chigurh

Psycho factor: The pudding-bowl haircut is scary enough, but Javier Bardem plays his coin-flipping killer so close to the vest that his silences speak volumes in this haunting film by Ethan and Joel Coen.